DE2318809A1 - Pfropfcopolymere und verfahren zu ihrer herstellung - Google Patents
Pfropfcopolymere und verfahren zu ihrer herstellungInfo
- Publication number
- DE2318809A1 DE2318809A1 DE19732318809 DE2318809A DE2318809A1 DE 2318809 A1 DE2318809 A1 DE 2318809A1 DE 19732318809 DE19732318809 DE 19732318809 DE 2318809 A DE2318809 A DE 2318809A DE 2318809 A1 DE2318809 A1 DE 2318809A1
- Authority
- DE
- Germany
- Prior art keywords
- molecular weight
- polymerizable
- polymer
- monomers
- macromolecular
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 229920000578 graft copolymer Polymers 0.000 title claims description 189
- 238000004519 manufacturing process Methods 0.000 title claims description 85
- 239000000178 monomer Substances 0.000 claims description 417
- 229920000642 polymer Polymers 0.000 claims description 302
- 239000004793 Polystyrene Substances 0.000 claims description 222
- 229920002223 polystyrene Polymers 0.000 claims description 222
- -1 allyl acrylates Chemical class 0.000 claims description 149
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 112
- 229920001577 copolymer Polymers 0.000 claims description 99
- 238000000034 method Methods 0.000 claims description 74
- 239000000203 mixture Substances 0.000 claims description 72
- 238000006243 chemical reaction Methods 0.000 claims description 69
- 238000009826 distribution Methods 0.000 claims description 66
- 239000004698 Polyethylene Substances 0.000 claims description 63
- 229920000573 polyethylene Polymers 0.000 claims description 63
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical class CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 56
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 52
- 150000001875 compounds Chemical class 0.000 claims description 52
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 51
- 239000005977 Ethylene Substances 0.000 claims description 51
- 238000007334 copolymerization reaction Methods 0.000 claims description 51
- 229910052757 nitrogen Inorganic materials 0.000 claims description 43
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 41
- 229920001195 polyisoprene Polymers 0.000 claims description 35
- 239000003999 initiator Substances 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 229920001169 thermoplastic Polymers 0.000 claims description 27
- 239000004416 thermosoftening plastic Substances 0.000 claims description 27
- 229920002554 vinyl polymer Polymers 0.000 claims description 25
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 21
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 20
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 20
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 18
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 18
- 150000002148 esters Chemical class 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 18
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 claims description 18
- 230000008569 process Effects 0.000 claims description 16
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 15
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 14
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 14
- 125000000129 anionic group Chemical group 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 239000004800 polyvinyl chloride Substances 0.000 claims description 14
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 14
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 13
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 13
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 12
- 125000003700 epoxy group Chemical group 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 229910052744 lithium Inorganic materials 0.000 claims description 12
- 239000011976 maleic acid Substances 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 11
- 150000001993 dienes Chemical class 0.000 claims description 11
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 11
- 229920002857 polybutadiene Polymers 0.000 claims description 11
- 239000005062 Polybutadiene Substances 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 10
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 claims description 10
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims description 9
- XJELOQYISYPGDX-UHFFFAOYSA-N ethenyl 2-chloroacetate Chemical compound ClCC(=O)OC=C XJELOQYISYPGDX-UHFFFAOYSA-N 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 8
- 239000002685 polymerization catalyst Substances 0.000 claims description 8
- 125000005068 thioepoxy group Chemical group S(O*)* 0.000 claims description 8
- 150000007513 acids Chemical class 0.000 claims description 7
- 150000008064 anhydrides Chemical class 0.000 claims description 7
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 6
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 6
- 150000001450 anions Chemical class 0.000 claims description 6
- 229920001155 polypropylene Polymers 0.000 claims description 6
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 claims description 5
- 239000004743 Polypropylene Substances 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 5
- 150000005840 aryl radicals Chemical class 0.000 claims description 5
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 claims description 5
- 239000012948 isocyanate Substances 0.000 claims description 5
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- 229920001567 vinyl ester resin Polymers 0.000 claims description 5
- HXGDTGSAIMULJN-UHFFFAOYSA-N acenaphthylene Chemical compound C1=CC(C=C2)=C3C2=CC=CC3=C1 HXGDTGSAIMULJN-UHFFFAOYSA-N 0.000 claims description 4
- 150000002513 isocyanates Chemical class 0.000 claims description 4
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims description 4
- 150000002825 nitriles Chemical class 0.000 claims description 4
- 229920002239 polyacrylonitrile Polymers 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- FCYVWWWTHPPJII-UHFFFAOYSA-N 2-methylidenepropanedinitrile Chemical compound N#CC(=C)C#N FCYVWWWTHPPJII-UHFFFAOYSA-N 0.000 claims description 3
- 125000005907 alkyl ester group Chemical group 0.000 claims description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 3
- MTZUIIAIAKMWLI-UHFFFAOYSA-N 1,2-diisocyanatobenzene Chemical class O=C=NC1=CC=CC=C1N=C=O MTZUIIAIAKMWLI-UHFFFAOYSA-N 0.000 claims description 2
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 claims description 2
- CWRYPZZKDGJXCA-UHFFFAOYSA-N acenaphthalene Natural products C1=CC(CC2)=C3C2=CC=CC3=C1 CWRYPZZKDGJXCA-UHFFFAOYSA-N 0.000 claims description 2
- 150000001299 aldehydes Chemical class 0.000 claims description 2
- 150000005215 alkyl ethers Chemical class 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 229920006158 high molecular weight polymer Polymers 0.000 claims description 2
- 150000007519 polyprotic acids Polymers 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims 2
- WHNPOQXWAMXPTA-UHFFFAOYSA-N 3-methylbut-2-enamide Chemical compound CC(C)=CC(N)=O WHNPOQXWAMXPTA-UHFFFAOYSA-N 0.000 claims 1
- 150000003926 acrylamides Chemical class 0.000 claims 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims 1
- 229920002959 polymer blend Polymers 0.000 claims 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 160
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 115
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 83
- 238000006116 polymerization reaction Methods 0.000 description 76
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 66
- 239000000047 product Substances 0.000 description 54
- 238000007792 addition Methods 0.000 description 47
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
- 239000003054 catalyst Substances 0.000 description 37
- 239000002904 solvent Substances 0.000 description 37
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 36
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 31
- 238000004458 analytical method Methods 0.000 description 30
- 238000005227 gel permeation chromatography Methods 0.000 description 28
- 230000000704 physical effect Effects 0.000 description 28
- 229930195733 hydrocarbon Natural products 0.000 description 26
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 229920001519 homopolymer Polymers 0.000 description 21
- 150000002430 hydrocarbons Chemical class 0.000 description 21
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 21
- 239000000463 material Substances 0.000 description 21
- 230000009257 reactivity Effects 0.000 description 21
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 20
- 239000012071 phase Substances 0.000 description 20
- 229920003023 plastic Polymers 0.000 description 20
- 239000004033 plastic Substances 0.000 description 20
- 150000003254 radicals Chemical class 0.000 description 20
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 19
- 239000003795 chemical substances by application Substances 0.000 description 18
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 18
- 239000004215 Carbon black (E152) Substances 0.000 description 17
- 230000015572 biosynthetic process Effects 0.000 description 17
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 16
- 238000003756 stirring Methods 0.000 description 16
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
- 239000012153 distilled water Substances 0.000 description 15
- 229910052751 metal Inorganic materials 0.000 description 15
- 239000002184 metal Substances 0.000 description 15
- 229920002451 polyvinyl alcohol Polymers 0.000 description 15
- 238000012360 testing method Methods 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 13
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 13
- 239000005266 side chain polymer Substances 0.000 description 13
- 239000004711 α-olefin Substances 0.000 description 13
- 239000004593 Epoxy Substances 0.000 description 12
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 12
- 239000011521 glass Substances 0.000 description 11
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- 239000013078 crystal Substances 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 229910052783 alkali metal Inorganic materials 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 229920000098 polyolefin Polymers 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- PGOLTJPQCISRTO-UHFFFAOYSA-N vinyllithium Chemical compound [Li]C=C PGOLTJPQCISRTO-UHFFFAOYSA-N 0.000 description 9
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 8
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- 230000007423 decrease Effects 0.000 description 8
- 125000005442 diisocyanate group Chemical group 0.000 description 8
- 229920000126 latex Polymers 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 7
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 7
- 239000004372 Polyvinyl alcohol Substances 0.000 description 7
- 238000005275 alloying Methods 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 238000012718 coordination polymerization Methods 0.000 description 7
- 230000002349 favourable effect Effects 0.000 description 7
- 150000004820 halides Chemical class 0.000 description 7
- 239000004816 latex Substances 0.000 description 7
- 238000002103 osmometry Methods 0.000 description 7
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 7
- 150000002978 peroxides Chemical class 0.000 description 7
- 229920001485 poly(butyl acrylate) polymer Polymers 0.000 description 7
- 229920005638 polyethylene monopolymer Polymers 0.000 description 7
- 230000002829 reductive effect Effects 0.000 description 7
- SLBOQBILGNEPEB-UHFFFAOYSA-N 1-chloroprop-2-enylbenzene Chemical compound C=CC(Cl)C1=CC=CC=C1 SLBOQBILGNEPEB-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000013459 approach Methods 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 229920001971 elastomer Polymers 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 238000010348 incorporation Methods 0.000 description 6
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 229920003251 poly(α-methylstyrene) Polymers 0.000 description 6
- 239000011591 potassium Substances 0.000 description 6
- 238000011084 recovery Methods 0.000 description 6
- 239000001488 sodium phosphate Substances 0.000 description 6
- 239000003381 stabilizer Substances 0.000 description 6
- JBIQAPKSNFTACH-UHFFFAOYSA-K vanadium oxytrichloride Chemical compound Cl[V](Cl)(Cl)=O JBIQAPKSNFTACH-UHFFFAOYSA-K 0.000 description 6
- 239000012808 vapor phase Substances 0.000 description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 5
- 150000001336 alkenes Chemical group 0.000 description 5
- 239000003963 antioxidant agent Substances 0.000 description 5
- 230000009286 beneficial effect Effects 0.000 description 5
- 229920005549 butyl rubber Polymers 0.000 description 5
- 238000010538 cationic polymerization reaction Methods 0.000 description 5
- 230000006835 compression Effects 0.000 description 5
- 238000007906 compression Methods 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 5
- 229910000397 disodium phosphate Inorganic materials 0.000 description 5
- 235000019800 disodium phosphate Nutrition 0.000 description 5
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 5
- 150000002334 glycols Chemical class 0.000 description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 239000011159 matrix material Substances 0.000 description 5
- 229910052700 potassium Inorganic materials 0.000 description 5
- 239000005060 rubber Substances 0.000 description 5
- 239000010935 stainless steel Substances 0.000 description 5
- 229910001220 stainless steel Inorganic materials 0.000 description 5
- 230000001954 sterilising effect Effects 0.000 description 5
- 238000004659 sterilization and disinfection Methods 0.000 description 5
- 238000010557 suspension polymerization reaction Methods 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 4
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Classifications
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G85/00—General processes for preparing compounds provided for in this subclass
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/30—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule
- C08C19/42—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with metals or metal-containing groups
- C08C19/44—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with metals or metal-containing groups of polymers containing metal atoms exclusively at one or both ends of the skeleton
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/04—Polymers provided for in subclasses C08C or C08F
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6204—Polymers of olefins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Graft Or Block Polymers (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00244205A US3832423A (en) | 1971-02-22 | 1972-04-14 | Chemically joined, phase separated graft copolymers having hydrocarbon polymeric backbones |
| US28209972A | 1972-08-21 | 1972-08-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2318809A1 true DE2318809A1 (de) | 1973-10-31 |
| DE2318809C2 DE2318809C2 (enrdf_load_stackoverflow) | 1987-08-06 |
Family
ID=26936387
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732318809 Granted DE2318809A1 (de) | 1972-04-14 | 1973-04-13 | Pfropfcopolymere und verfahren zu ihrer herstellung |
Country Status (12)
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2500494A1 (de) * | 1974-01-11 | 1975-07-17 | Cpc International Inc | Neue pfropfmischpolymerisate und verfahren zu ihrer herstellung |
| EP0303087A3 (de) * | 1987-08-04 | 1991-04-24 | Bayer Ag | Polymere Dihydroxyverbindungen und ihre Verwendung als Stabilisatoren für Polymere |
| EP0374553A3 (de) * | 1988-12-15 | 1991-05-15 | Bayer Ag | Verfahren zur Herstellung von Polymeren mit phenolischen Hydroxylendgruppen |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8701021D0 (en) * | 1987-01-19 | 1987-02-18 | Pethrick R A M | Polymeric materials |
| JP2802076B2 (ja) * | 1988-08-31 | 1998-09-21 | 三菱レイヨン株式会社 | くし形共重合体の製造方法 |
| JPH0416368U (enrdf_load_stackoverflow) * | 1990-05-29 | 1992-02-10 | ||
| FR2750321B1 (fr) * | 1996-06-28 | 1998-07-31 | Oreal | Utilisation en cosmetique de copolymeres a squelette flexible, greffes par des macromonomeres hydrophobes et rigides ; compositions mises en oeuvre |
| US5942243A (en) * | 1996-11-12 | 1999-08-24 | Polytherapeutics, Inc. | Mucoadhesive compositions for administration of biologically active agents to animal tissue |
| CA2333998A1 (en) * | 1998-06-11 | 1999-12-16 | The Dow Chemical Company | Photocurable elastomeric compositions |
| WO1999065963A1 (fr) * | 1998-06-19 | 1999-12-23 | Kaneka Corporation | Procede de fabrication d'un polymere ramifie et polymere correspondant |
| US20060281888A1 (en) * | 2005-06-13 | 2006-12-14 | Alcon, Inc. | Ophthalmic and otorhinolaryngological device materials |
| TW200816966A (en) * | 2006-07-21 | 2008-04-16 | Alcon Mfg Ltd | Low-tack ophthalmic and otorhinolaryngological device materials |
| EP1947125A1 (en) | 2007-01-16 | 2008-07-23 | Cognis IP Management GmbH | Grafted Polymers |
| TW201305728A (zh) * | 2011-07-20 | 2013-02-01 | Chi Mei Corp | 感光性樹脂組成物及其應用 |
| JP6868395B2 (ja) * | 2014-06-20 | 2021-05-12 | ユニバーシティ オブ テネシー リサーチ ファウンデーションＵｎｉｖｅｒｓｉｔｙ Ｏｆ Ｔｅｎｎｅｓｓｅｅ Ｒｅｓｅａｒｃｈ Ｆｏｕｎｄａｔｉｏｎ | 乳化重合によるマルチグラフトコポリマー超エラストマー |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1093472A (en) * | 1964-01-02 | 1967-12-06 | Monsanto Co | Anionic polymerisation process |
| ZA72820B (en) * | 1971-02-22 | 1972-10-25 | Cpc International Inc | Polymers and process of producing |
-
1973
- 1973-03-26 GB GB1451673A patent/GB1432782A/en not_active Expired
- 1973-03-26 GB GB3468375A patent/GB1432783A/en not_active Expired
- 1973-03-30 CA CA167,581A patent/CA1037636A/en not_active Expired
- 1973-04-12 SE SE7305227A patent/SE417101B/xx unknown
- 1973-04-13 NL NL7305190A patent/NL164866C/xx not_active IP Right Cessation
- 1973-04-13 FR FR7313452A patent/FR2197908B1/fr not_active Expired
- 1973-04-13 DD DD17941073A patent/DD111685A5/xx unknown
- 1973-04-13 DD DD17021373A patent/DD108102A5/xx unknown
- 1973-04-13 IT IT2301273A patent/IT982767B/it active
- 1973-04-13 ES ES413669A patent/ES413669A1/es not_active Expired
- 1973-04-13 DE DE19732318809 patent/DE2318809A1/de active Granted
- 1973-04-13 CH CH536373A patent/CH606120A5/xx not_active IP Right Cessation
- 1973-04-14 JP JP4185073A patent/JPS5410996B2/ja not_active Expired
- 1973-04-14 CS CS473876A patent/CS194179B2/cs unknown
- 1973-04-14 CS CS473776A patent/CS194178B2/cs unknown
-
1975
- 1975-08-01 ES ES439947A patent/ES439947A1/es not_active Expired
- 1975-12-12 JP JP14748375A patent/JPS51125186A/ja active Granted
-
1976
- 1976-05-14 SE SE7605560A patent/SE425396B/xx not_active IP Right Cessation
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2500494A1 (de) * | 1974-01-11 | 1975-07-17 | Cpc International Inc | Neue pfropfmischpolymerisate und verfahren zu ihrer herstellung |
| DK151816B (da) * | 1974-01-11 | 1988-01-04 | Research Corp | Hydrogel med anvendelighed som medicinsk hydrogel og fremgangsmaade til fremstilling deraf |
| EP0303087A3 (de) * | 1987-08-04 | 1991-04-24 | Bayer Ag | Polymere Dihydroxyverbindungen und ihre Verwendung als Stabilisatoren für Polymere |
| EP0374553A3 (de) * | 1988-12-15 | 1991-05-15 | Bayer Ag | Verfahren zur Herstellung von Polymeren mit phenolischen Hydroxylendgruppen |
Also Published As
| Publication number | Publication date |
|---|---|
| SE417101B (sv) | 1981-02-23 |
| CA1037636A (en) | 1978-08-29 |
| JPS4930462A (enrdf_load_stackoverflow) | 1974-03-18 |
| SE7605560L (sv) | 1976-05-14 |
| DD111685A5 (enrdf_load_stackoverflow) | 1975-03-05 |
| IT982767B (it) | 1974-10-21 |
| GB1432782A (en) | 1976-04-22 |
| DD108102A5 (de) | 1974-09-05 |
| FR2197908B1 (enrdf_load_stackoverflow) | 1979-02-09 |
| JPS51125186A (en) | 1976-11-01 |
| CH606120A5 (enrdf_load_stackoverflow) | 1978-10-13 |
| DE2318809C2 (enrdf_load_stackoverflow) | 1987-08-06 |
| ES439947A1 (es) | 1977-03-01 |
| JPS5410996B2 (enrdf_load_stackoverflow) | 1979-05-11 |
| ES413669A1 (es) | 1976-07-16 |
| CS194178B2 (en) | 1979-11-30 |
| NL164866C (nl) | 1981-02-16 |
| FR2197908A1 (enrdf_load_stackoverflow) | 1974-03-29 |
| JPS5345358B2 (enrdf_load_stackoverflow) | 1978-12-06 |
| GB1432783A (en) | 1976-04-22 |
| SE425396B (sv) | 1982-09-27 |
| NL7305190A (enrdf_load_stackoverflow) | 1973-10-16 |
| NL164866B (nl) | 1980-09-15 |
| CS194179B2 (en) | 1979-11-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8127 | New person/name/address of the applicant |
Owner name: RESEARCH CORP., NEW YORK, N.Y., US |
|
| 8128 | New person/name/address of the agent |
Representative=s name: DEUFEL, P., DIPL.-WIRTSCH.-ING. DR.RER.NAT. SCHOEN |
|
| 8125 | Change of the main classification |
Ipc: C08L 27/06 |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition |